Reaktion #497191

Reaktionsgleichung

n-BuLi

bifuran

Bu3SnCl

→

1

Ausbeute 60.0%

2-(tributylstannyl)bifuran

Ausbeute 60.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   Sonstigeto reach room temperature
3. 3
   workup.STIRRINGstirred for 2 h
4. 4
   ExtraktionThe mixture was extracted with hexane
5. 5
   Trocknendried (MgSO4)
6. 6
   Sonstigeevaporated
7. 7
   SonstigeSeperation by chromatography

Vorschrift

A solution of n-BuLi (7.7 mL, of 2.5M in hexanes, 19.2 mmol, 1.3 equivalents) was added dropwise to a solution of bifuran (2 g, 14.9 mmol) in dry THF (100 mL) at −78° C. under N2. The mixture was allowed to come to room temperature and stirred for 1 h. To the white suspension was added dropwise Bu3SnCl (4 mL, 14.9 mmol) at 0° C. and the reaction was allowed to reach room temperature and stirred for 2 h. The mixture was extracted with hexane, dried (MgSO4) and evaporated. Seperation by chromatography using bacified silica (Et3N) and hexane gave 1 (3.8 g, 60% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 0.85-0.91 (t, J=7.3 Hz, 9H), 1.03-1.13 (m, 6H), 1.26-1.39 (m, 6H), 1.48-1.63 (m, 6H), 6.40-6.42 (m, 1H), 6.50 (d, J=3.3 Hz, 1H), 6.57 (dd, J=3.3, 6.0 Hz, 2H), 7.34 (dd, J=0.7, 1.8 Hz, 1H) ppm. 13C NMR (300 MHz, CDCl3): δ 10.2, 13.7, 27.2, 28.9, 104.6, 105.0, 111.3, 123.0, 141.4, 147.5, 151.0, 160.9 ppm

Quelle